3-Furaldehyde → (E)-3-styrylfuran

HRID 1460915Notes

Reaction equation

HRID 1460915 reaction equation
CC(C)([O-])C.[K+].C(C1C=COC=1)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[PH4+].[CH:35]([C:43]1[CH:47]=[CH:46][O:45][CH:44]=1)=[CH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.CCOCC.O>[CH:35](/[C:43]1[CH:47]=[CH:46][O:45][CH:44]=1)=[CH:36]\[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

9

Reactant 5

HCID 103513-FuraldehydeHCID 13097Triphenylphosphine OxideHCID 5460504PhosphoniumHCID 23665647Potassium tert-butoxideHCID 537983163-(2-Phenylethenyl)furan

Product 1

HCID 14326174(E)-3-styrylfuranYield 19%

Reagents, catalysts & solvents 3

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Potassium tert-butoxide (35.7 g) was added in one portion to a stirred suspension of benzyltriphenylphosphonium chloride (41.6 g) in ether (1 liter). After 1 hour, a solution of 3-formylfuran (17.5 g) in ether (60 ml) was added to the resulting orange mixture which was then stirred for 2 hours, poured into water, and extracted with ether. The extracts were washed with water, dried and concentrated to give a solid. Trituration of this solid with ether enabled much of the weakly-soluble triphenylphosphine oxide and excess phosphonium salt to be separated, and the ether-soluble fraction (37.06 g) was chromatographed using ether as eluent to give a mixture of (E)-- and (Z)-isomers of 3-styrylfuran (27 g) as a yellow solid. Crystallisation twice from methanol gave (E)-3-styrylfuran (5.12 g), mp 96° C., as a yellow solid.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customto give a solid
  6. customto be separated
  7. customthe ether-soluble fraction (37.06 g) was chromatographed
  8. customto give
  9. customCrystallisation twice from methanol

Sources & evidence

ORD record
ord-94514e62453d46a08e0a14fe5dceae41
Source dataset
uspto-grants-1991_12
Patent number
US05073184

Reaction notes

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